1. Field of the Invention
This invention is directed to organic compounds and is particularly concerned with a novel process for the preparation of 1-aminomethyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines and the intermediates thereof.
The novel process or products can be illustratively represented as follows: ##SPC3##
Wherein R' and R" are alkyl of 1 to 3 carbon atoms, inclusive or together ##EQU2## is pyrrolidino, piperidino, 4-methylpiperazino or morpholino.
The invention encompasses besides the process I.fwdarw. II.fwdarw. III.fwdarw.IV.fwdarw.V the novel intermediates of formulae II and IV above.
The more desirable intermediates of the type II have the more specific formula IIA: ##SPC4##
wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, or trifluoromethyl; wherein R.sub.2 is hydrogen, fluoro, or chloro; and wherein R.sub.3 is hydrogen, or fluoro if R.sub.2 is also fluoro.
The most desirable intermediates of type II are of the formula IIB: ##SPC5##
wherein R'.sub.1 and R'.sub.2 are hydrogen or chloro.
The more desirable products of formula IV have the more specific formula IVA: ##SPC6##
wherein R'.sub.0 and R".sub.0 are alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, or trifluoromethyl; wherein R.sub.2 is hydrogen, fluoro, chloro; and wherein R.sub.3 is hydrogen or fluoro, if R.sub.2 is also fluoro.
The most desirable intermediates of type IV have the specific formula IVB: ##SPC7##
wherein R'.sub.1 and R'.sub.2 are hydrogen or chlorine.
The process of this invention comprises: treating an equivalent of compound I with two equivalents of .alpha.-phthalimidoacetyl chloride or bromide in an inert organic solvent to obtain compound II; treating compound II with trifluoroacetic acid to obtain compound III; treating compound III with a dialkylmethyleneammonium chloride or bromide to obtain compound IV; and treating compound IV with hydrazine in ethanol to obtain compound V above.